Tailor-Made Holiday

Cuba - In Depth

Two weeks in the heart of Cuba

13 days

from £4,235pp (excluding flights)

Cocktails, soulful tunes and enough culture to sate any thirst. This in-depth journey to Cuba is a wonderful journey for those looking to get to the heart of this vibrant country. Vintage cars, art tours, mountain hikes and homestays. This itinerary really allows you to get to know the country and as John will testify, the new wave of accommodation is cutting edge, the food excellent, the people enchanting, the island fascinating and the zest for life infectious.

  • Cruise Havana's streets in an open top 1950's vintage car
  • Travel to the Bay of Pigs, home to the US invasion and explore the Zapata Peninsula, great for bird watching.
  • Visit the  UNESCO town of Trinidad, a mini Havana with fantastic live music
  • Stay with a local family for an insight into Cuban way of life.
  • Discover the Sugarmill Valley and the history of slavery in Cuba
  • Relax on Cayo Santa Maria

This journey takes you to the Cuba's capital Havana, where faded grandeur meets colonial charm. Cruise the streets by classic car taking in sites such as Revolution Square which hosted many a speech from Fidel Castro. Dine in local paladares, a gastronomic delight not known to many, before exploring the art galleries and superb nightlife of jazz and salsa.

Continue your journey to the Zapata Peninsula, a haven for wildlife both on land and in the water. Your host at Casa Ronel is a skilled diver and will be delighted to take you out snorkelling. He may even catch your supper. The museum at the Bay of Pigs is well worth a visit. Not only is it an important time in Cuban history, there is some fascinating memorabilia to view including tanks, mortar launches and an old British-made Hawker Sea Fury plane used by the Cuban military.

Further south is the delightful town of Trinidad. Its cobbled streets and faded pastel coloured houses reflect a time of great wealth. Magnificent mansions built by the Spanish from the time of the sugar barons stand in faded glory. Stay at Finca Kenia which is one of the oldest houses in Trinidad. Now restored by Kenia and her family, they have opened its doors offering bed & breakfast and a pool with a view.  During the day, visit the old sugar plantations or head up into the pretty hills of Topes de Collantes for fresher air and brisk mountain walks. Trinidad comes alive after dark in the music houses, where band after band perform and where the rum always flows.

This journey concludes on the beaches of Cayo Santo Maria off the north coast of Cuba. Relax with a book, or get involved in the water sports. The Melia Cayo Santa Maria has it all.

For a more detailed itinerary with great ideas on what to do and where to stay, please get in touch with our experts.

Price Excluding Flights £Flight cost from 
£ 4235 £ 660
  Click here to see what is included/excluded

what is included

  • All accommodation
  • Internal flights
  • International flights as detailed
  • Sightseeing with private guide as per the itinerary
  • Transfers as detailed

what is excluded

  • Gratuities
  • Travel Insurance
  • Visas


Itinerary at a glance

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Day 1

Fly London to Havana

You will be staying at Hotel Santa Isabel, Bed & Breakfast

Day 2

Old Havana Walking Tour
Half day walking tour of Old Havana. Walk in the footsteps of Havana´s colonial past visiting the four plazas of Old Havana, a UNESCO world heritage site. Visit Plaza de Armas, Plaza San Francisco de Asis, Plaza Vieja and Plaza de la Cathedral with your expert guide offering insightful history along the way.

Romantic, beautiful and fascinating, Havana is a must for anyone's visit to Cuba. Fortifications, colonial buildings and churches tell of a rich history, whilst a Communist regime and erosion from the sea lend a faded glory to the city. The old heart gives way to Soviet starkness, whilst the 1950s playground of Vedado, neighbours the historic mansions of Miramar. Quite simply, stunning.

Havana Art Tour
Leave your hotel with your guide for an Art Tour. You will visit 4 emerging Cuban artists in their studios. Get behind the façade and interact with this thriving community. We can adapt the visits depending on your particular interest. Photography, sculpture or painting. Specify whether you would like to see well known or up and coming artists.

You will be staying at Hotel Santa Isabel, Bed & Breakfast

Day 3

Havana Time to Yourself
Time to yourself to enjoy ’La Habana’.

Highlights of the old town include the Plaza de la Catedral, the Malecon lining the sea front, the Plaza de Armas and the Castillo del Morro.

There is also an excellent market during the weekend. However to see all sides of the city a visit to the Communist aspects such as the Plaza de la Revolucion and its concrete surroundings is a must.

Explore the streets of the old town, enjoy a Mojito in Hemingway’s favourite bar, listen to the jazz played in the plazas and watch the world and the 1950s cars go by.

Classic Car drive
4 hour drive in a vintage open top car in a genuine 1959 Buick.

Your tour can be tailored to take in the highlights of Havana as well as themed around Hemingway. En route you´ll be able to take panoramic shots from El Morro, the fortress at the mouth of Havana harbour, the Malecon, iconic cinemas such as La Rampa & Chaplin and the impressive Bacardi building, Revolution Square; home to a large image of Che Guevara, the woods in Kholy, Playa and the river Almendares.

Cruising with the roof down along the malecon at sunset while listening to Sinatra is a magical experience.

You will be staying at Hotel Santa Isabel, Bed & Breakfast

Day 4

Drive from Havana to Playa Giron (Road Journey)

You will be staying at Casa Ronel, Bed & Breakfast

Day 5

Guided walk in the Cienega de Zapata
Today visit the woodland area of the Cienega Zapata. Travel by horse and cart into the forest and then continue on foot with your guide as he explains the unique geology and ecology of this vast national park. This is a great opportunity for bird watching as some of the most important national species live in this area. You might even get to see the famous Cuban species of rodent known as Jutia (Tree Rat).

Drive from Playa Giron to Trinidad (Road Journey)

Trinidad is arguably the most beautiful town in Cuba. Said to be dozing in an 18th century time warp and where the pace of life remains as slow, it is a perfect relic of Spanish colonialism with plazas, churches, palaces and cobbled streets. Trinidad is also gateway to several Caribbean beaches, as well as and the trekking trails and sugar mills of the Escambray Mountains.

You will be staying at Finca Kenia, Bed & Breakfast

Day 6

Walking tour of Trinidad
Meet your guide for a three hour walking tour of Trinidad’s historic city centre. Your guide will talk you through the history of Trinidad by visiting its architectural high points before finishing at Bar Canchancharra for a local mojito of wild mint, honey and rum and, of course, some Cuban music.

Sugarmill Valley tour
This afternoon explore the area outside Trinidad, in particular the Sugarmill Valley in the Sierra Escambray, one of the most beautiful landscapes in Cuba. Learn about the sugarcane industry and climb up the famous Iznaga slave tower, which was built to control the slave workforce. The tour focuses on slave history, the working plantation homes of the sugar barons and looks at the enormous impact sugar production had on this area.

You will be staying at Finca Kenia, Bed & Breakfast

Day 7

Truck Safari to Topes de Collantes
Ride up to the Escambray mountains in ex soviet military jeeps or trucks. Go up to Guanayara and trek trough the tropical forest of Topes. Bird watching and an opportunity for swimming at the waterfall make this a must for nature lovers. For those interested in Revolution history, lunch (included) is at the house of ''La Gallega'' who has an important friendship with Fidel Castro. (Please note that in high season the government supplier of the transport may change from private jeep transport to group truck transport, sometimes without any notification. While we do our utmost to ensure that you know which type of transport you will be using, it is not always possible due to last minute changes).

You will be staying at Finca Kenia, Bed & Breakfast

Day 8

Drive from Trinidad to Cayo Santa Maria (Road Journey)

You will be staying at Hotel Melia Cayo Santa Maria, All inclusive

Day 9

At leisure on Cayo Santa Maria
Enjoy the beautiful setting of Cayo Santa Maria on the shores of the Caribbean Sea. Explore the stretches of white sand which is part of a biosphere reserve. Of course you can also relax by the pool or treat yourself to some pampering at the spa.

You will be staying at Hotel Melia Cayo Santa Maria, All inclusive

Day 10

You will be staying at Hotel Melia Cayo Santa Maria, All inclusive

Day 11

Day at leisure in Cayo Santa Maria

You will be staying at Hotel Santa Isabel, Bed & Breakfast

Day 12

Fly Havana to London


Below you can see some of the wonderful places we recommend you stay on your journey.

Hotel Santa Isabel

Hotel Santa Isabel

Once a magnificent mansion owned by Count Santovenia, the Santa Isabel was established as a hotel back in 1867....

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Finca Kenia

Finca Kenia

Built in the second half of the nineteenth century, on the edge of Santa Rosa Valley, Finca Kenia (also known as La Casona) is one of the oldest houses in Trinidad....

View Accommodation

For a more detailed itinerary with great ideas on what to do and where to stay, please get in touch with our experts.

Destination Experts

Our experts have unrivalled firsthand knowledge of Cuba

John Faithfull, Travel Expert

"Personalised service. Seemed to really want to get it right for us. Very impressed when I first called and John spent 40 minutes finding out what we wanted to do and tailoring it for us."

"The expertise that John has really gave us faith in where we were going, the regions, the hotels, the trips. John knew about it all, he described them in detail, and when we asked for different regions he was straight in there with suggestions and ideas. The way the whole trip was planned and presented to us, never any pressure to book or any problem to change plans /ideas."

"John Faithful was wonderfully helpful and conscientious in arranging the itinerary and was always ready to suggest alternatives or rearrange matters without any hesitation; this and his detailed knowledge gave one great confidence."

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For a more detailed itinerary with great ideas on what to do and where to stay, please get in touch with our experts.

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